Chiassa Superiore Vacation Rentals from CA $81: Short-Term Rentals for 2026

Q: What are some of the best vacation rentals that Chiassa Superiore has to offer?

Holiday Home in Umbria with Pool : Located near Chiassa Superiore, this vacation home rental offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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Our top choices for Chiassa Superiore vacation rentals

1. iConic Wellness Resort

Arezzo

Wade

CA $124 total

includes taxes & fees

Dec 2 - Dec 3

A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

2. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

CA $121 total

includes taxes & fees

Nov 11 - Nov 12

A balcony with potted plants and a view of a cityscape.

3. Cameracaffè Centro

Arezzo Centro Storico

Steven

CA $148 total

includes taxes & fees

Nov 5 - Nov 6

A modern hotel room with large windows, a bed, a desk, and a chair.

4. B&B 52cento

Arezzo Centro Storico

Tina

CA $126 total

includes taxes & fees

Nov 12 - Nov 13

A bedroom with a large bed, a chandelier, a mirror, and plants.

5. Bibi Boutique

Arezzo Centro Storico

Carol

CA $137 total

includes taxes & fees

Nov 5 - Nov 6

A stone building with arched windows and a gravel driveway.

6. Villa La Ginestra

Subbiano

Philippe

CA $164 total

includes taxes & fees

Nov 5 - Nov 6

A stone building with a tiled roof, surrounded by lush green fields and mountains in the background.

7. Locanda del Viandante

Anghiari

Kenneth

CA $196 total

includes taxes & fees

Nov 6 - Nov 7

A cozy living room with a stone wall, a wine rack, and two sofas.

8. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

CA $177 total

includes taxes & fees

Nov 6 - Nov 7

A narrow stone-walled room with a wooden table and blue upholstered chairs.

9. Allegra Toscana - Affittacamere & Guest House Arezzo

Arezzo Centro Storico

Justin

CA $154 total

includes taxes & fees

Nov 10 - Nov 11

A wooden table with two chairs on a balcony, overlooking a lush green landscape with trees and hills.

10. Casa Vacanze Le Fornaci

Pergine Valdarno

Lisette

CA $172 total

includes taxes & fees

Nov 16 - Nov 17

A dining area with a wooden table and chairs, stone walls, and arched doorways.

11. Wonderful private villa with private pool, A/C, WIFI, TV, pets allowed and parking, close to Are...

Subbiano

Anonymous traveller

CA $808 total

includes taxes & fees

Dec 2 - Dec 3

An arched stone bridge with a white building on the right, featuring a balcony with plants.

12. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

CA $160 total

includes taxes & fees

Nov 14 - Nov 15

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

13. Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

Kristina

CA $244 total

includes taxes & fees

Nov 13 - Nov 14

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

14. Castello di Gargonza

Monte San Savino

Iain

CA $430 total

includes taxes & fees

Nov 5 - Nov 6

A narrow street with historic buildings, a balcony with potted plants, and a no parking sign.

15. Dolce Rosa Centro Storico

Sansepolcro

Sergio

CA $89 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with a large bed, a fireplace, and a brick ceiling.

16. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $172 total

includes taxes & fees

Nov 22 - Nov 23

17. Palazzo Tarlati Residenza d'Epoca

Civitella in Val di Chiana

"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...

Marco

CA $250 total

includes taxes & fees

Nov 7 - Nov 8

A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

18. San Michele al Borgo

Castiglion Fiorentino

Vern

CA $211 total

includes taxes & fees

Nov 8 - Nov 9

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

19. B&B Piccolo Hotel

Cortona Old Town

mansoor

CA $222 total

includes taxes & fees

Nov 5 - Nov 6

A sectional sofa with a chaise, positioned against a plain wall, on a wooden floor.

20. La Corte dei Servi - Locazione Turistica

Sansepolcro

CA $276 total

includes taxes & fees

Nov 11 - Nov 12

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Find vacation rentals that suit your style

Top Chiassa Superiore Hotel Reviews

A stone villa with a swimming pool, outdoor seating, and a well-lit patio area.

Chimera Tuscany Resort

Arezzo

10/10 Excellent

Greg

A greenhouse-style dining area with tables and chairs, surrounded by greenery and string lights.

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Excellent

erik

A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

Hotel Le Capanne

Arezzo

10/10 Excellent

Jo

A stone building with a garden of lavender at dusk.

Agriturismo Cuprena

Arezzo

10/10 Excellent

philip

iConic Wellness Resort

Arezzo

10/10 Excellent

Booked for a one night stay, not realizing that this was an actual spa/resort. Paolo the owner greeted us and was a real pleasure. He is very enthusastic about his property and offered us a full tour. The property is stunning. A bit out of the way from downtown Arezzo, but is definitely worth a visit. I would stay again and recommend now that I have a full scope of the services offered. Booking the property online, we were more looking for a place to lay our head for the night and in hindsight...

Wendy

A brick archway leading to a courtyard with a statue, a dartboard, and a bicycle.

B&B Villa La Nussa

Capolona

10/10 Excellent

What a wonderful old building this was. First built in 1475 and as a monastery, it is owned and run by a fabulous couple who are very helpful and special people. Very knowledgeable about the whole Tuscany area. Recommended many places. Breakfast was wonderful. Great big yard with many beautiful fruit trees. A very nice pool. A very terrace and sitting area. Wifi worked fine in one area of the public area but not in the room. Great value for the price.

Stan

A spacious hallway with a round wooden coffee table, a chandelier, and potted plants.

Residenza d'epoca Luca Pacioli

Sansepolcro

10/10 Excellent

Denis

A modern interior with a decorative wall, a bed with pillows, and a small table with a lamp.

Il Gentiluomo Hotel & SPA

Arezzo

10/10 Excellent

Better than expected for the value. A few small cosmetic items. But great value. Great breakfast that’s half the cost at the desk vs online. Does have a trickle charger for EV’s in the garage but it is very limited for charging 25% in 12 hours. Address doesn’t seem to align with Hotels.com address It took 2 hours to find and isn’t marked on the buildings upper structure. But, well worth finding for Comfort, friendliness and quality of the hotel. And, I’m a Canadian Builder and Realtor so I’m...

Anonymous traveller

A view from a window with sheer curtains, a wooden chair, and a glimpse of a landscape with trees and a building.

I Salici Agriturismo

Pergine Valdarno

10/10 Excellent

Chanel

Find out more about Chiassa Superiore

Everything you need to know about Chiassa Superiore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chiassa Superiore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chiassa Superiore vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chiassa Superiore vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chiassa Superiore. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chiassa Superiore vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chiassa Superiore vacation rentals we have selected for you start as low as CA $81 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chiassa Superiore rentals

At Expedia, we put the best Chiassa Superiore vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chiassa Superiore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chiassa Superiore vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chiassa Superiore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Chiassa Superiore?

Yes, there are vacation rentals near popular sights in Chiassa Superiore, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Chiassa Superiore has to offer?

Holiday Home in Umbria with Pool: Located near Chiassa Superiore, this vacation home rental offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Chiassa Superiore?

While exploring the area, visit family-friendly sights like Aboca Museum, or get outside and enjoy nature at Piazza Guido Monaco. In the larger area, you’ll find Castelnuovo di Subbiano and Cathedral of Saints Peter and Donato.

What’s a vacation rental in Chiassa Superiore like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Chiassa Superiore. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.

Chiassa Superiore Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chiassa Superiore vacation rentals

1. iConic Wellness Resort

2. Limehome Arezzo Duomo

3. Cameracaffè Centro

4. B&B 52cento

5. Bibi Boutique

6. Villa La Ginestra

7. Locanda del Viandante

8. Villa Cassia di Baccano

9. Allegra Toscana - Affittacamere & Guest House Arezzo

10. Casa Vacanze Le Fornaci

11. Wonderful private villa with private pool, A/C, WIFI, TV, pets allowed and parking, close to Are...

12. Locanda Antico Borgo

13. Relais Villa Belpoggio - Residenza d'Epoca

14. Castello di Gargonza

15. Dolce Rosa Centro Storico

16. DormiVeglia B&B

17. Palazzo Tarlati Residenza d'Epoca

18. San Michele al Borgo

19. B&B Piccolo Hotel

20. La Corte dei Servi - Locazione Turistica

Find vacation rentals that suit your style

Top Chiassa Superiore Hotel Reviews

Chimera Tuscany Resort

10/10 Excellent

Find out more about Chiassa Superiore

Chiassa Superiore vacation rentals: An excellent choice for every season

How to find incredible deals on Chiassa Superiore rentals

Frequently Asked Questions

Can I find a vacation rental in Chiassa Superiore?

What are some of the best vacation rentals that Chiassa Superiore has to offer?

What’s there to see and do in Chiassa Superiore?

What’s a vacation rental in Chiassa Superiore like?